MARINE TOXINS AND VENOMOUS AND POISONOUS MARINE ANMALS
267
and secondary alcohols, and the Benedict test for reducing sugars
have all been negative.
Wintersteiner et al. (see Schantz, 1960) have shown that oxidation of
the poison in a mild alkaline solution exposed to the air reduces the
toxicity in direct proportion to the oxygen uptake. The mixture had
a molecular extinction of 6000 to 7000 in ultraviolet at 235 and 333 mp.
Further studies indicated that the unsaturated bond is probably
involved in the toxic structure of the poison and would appear to be the
point at which oxidation of the poison occurs when exposed to air at
pH values above 7. With strong oxidation, Sakaguchi-positive compounds are obtained. Guanidoproprionic acid, urea, ammonia, carbon
dioxide and guanidine have been isolated as oxidation products.
A comparison of the properties of the poison from mussels and
clams (Schantz et al., 1957) with those from dinoflagellates indicated
that the toxins had very similar properties. Subsequently, in chromatographic studies, Burke and msociates (1960) demonstrated that the
toxin from Gonyauk catenella and that from mussels move in a similar
manner. In 1962, Schantz and colleagues isolated the toxin in a purified
form from G. catenella; they found the physical, chemical and gross
physiopharmacological properties of the poison to be identical with those
of Mytilus californianus and Saxidomas giganteus.
It has been suggested that the toxin might be formed by a bacterium with the protistan but a number of investigators have isolated
the dinoflagellates free of bacteria and demonstrated that the organism
is still capable of producing the poison. This finding indicates that the
toxin is a metabolic product and not the result of a symbiotic effect of
bacteria.
The evidence to date suggests that ring structures are present and
that several of the nitrogen atoms are involved in a heterocyclic
structure. It appears that there are no aromatic structures, and no
conjugate unsaturation or isolated carbonyl groups. Titration suggests
that one of the two basic groups may be a guanidine (pK, 11.5) and the
other an amine (pK, 8.1).
I n reviewing the chemistry of " prymnesin ", the toxin from
Prymnesium parvum N. Carter (a flagellate found in fresh, brackish
and marine waters), Parnas (1963) notes that the poison is nondializable,
poorly soluble in water, insoluble in carbon tetrachloride, chloroform,
benzene, ether, ethyl acetate and n-butanol. It absorbs on activated
charcoal, kaolin and Mg(0H)z ; but does not absorb on anion and cation
exchangers. It gives a positive reaction for carbohydrates and to
ninhydrin. Prymnesin prepared in the dark has a typical absorption
at 260 mp, which following irradiation falls to 240 mp. The biological
267
and secondary alcohols, and the Benedict test for reducing sugars
have all been negative.
Wintersteiner et al. (see Schantz, 1960) have shown that oxidation of
the poison in a mild alkaline solution exposed to the air reduces the
toxicity in direct proportion to the oxygen uptake. The mixture had
a molecular extinction of 6000 to 7000 in ultraviolet at 235 and 333 mp.
Further studies indicated that the unsaturated bond is probably
involved in the toxic structure of the poison and would appear to be the
point at which oxidation of the poison occurs when exposed to air at
pH values above 7. With strong oxidation, Sakaguchi-positive compounds are obtained. Guanidoproprionic acid, urea, ammonia, carbon
dioxide and guanidine have been isolated as oxidation products.
A comparison of the properties of the poison from mussels and
clams (Schantz et al., 1957) with those from dinoflagellates indicated
that the toxins had very similar properties. Subsequently, in chromatographic studies, Burke and msociates (1960) demonstrated that the
toxin from Gonyauk catenella and that from mussels move in a similar
manner. In 1962, Schantz and colleagues isolated the toxin in a purified
form from G. catenella; they found the physical, chemical and gross
physiopharmacological properties of the poison to be identical with those
of Mytilus californianus and Saxidomas giganteus.
It has been suggested that the toxin might be formed by a bacterium with the protistan but a number of investigators have isolated
the dinoflagellates free of bacteria and demonstrated that the organism
is still capable of producing the poison. This finding indicates that the
toxin is a metabolic product and not the result of a symbiotic effect of
bacteria.
The evidence to date suggests that ring structures are present and
that several of the nitrogen atoms are involved in a heterocyclic
structure. It appears that there are no aromatic structures, and no
conjugate unsaturation or isolated carbonyl groups. Titration suggests
that one of the two basic groups may be a guanidine (pK, 11.5) and the
other an amine (pK, 8.1).
I n reviewing the chemistry of " prymnesin ", the toxin from
Prymnesium parvum N. Carter (a flagellate found in fresh, brackish
and marine waters), Parnas (1963) notes that the poison is nondializable,
poorly soluble in water, insoluble in carbon tetrachloride, chloroform,
benzene, ether, ethyl acetate and n-butanol. It absorbs on activated
charcoal, kaolin and Mg(0H)z ; but does not absorb on anion and cation
exchangers. It gives a positive reaction for carbohydrates and to
ninhydrin. Prymnesin prepared in the dark has a typical absorption
at 260 mp, which following irradiation falls to 240 mp. The biological